The aspidosperma alkaloids are an ever-growing class of indole alkaloids which posses complex architectures and a wide array of biological activity. For example, vincristine and vinblastine have long been used as cancer therapeutics. The following research proposal describes a novel cascade approach to these alkaloids. Through the coupling of an intramolecular Diels-Alder cyclization with an amino-Cope rearrangement we hope to set the four contiguous stereocenters in the aspidosperma alkaloids during a single synthetic step. This approach has the potential to be the shortest synthesis of these alkaloids to date. In addition, it should be readily adaptable to the synthesis many of the aspidosperma alkaloids. Through the development of this new methodology we hope to further our understanding of both the intramolecular Diels-Alder cyclization and the amino-Cope rearrangement, two very powerful synthetic transformations.